How To Convince Your Boss You Need A (New) Project Management Tool

So you found a new project management tool, and it’s a winner. It has the planning capabilities and collaboration tools you need to get your projects from idea to delivery. The visuals are great, the features are exactly what you need, and the integrations are tailor made for you. But there’s a problem: your boss has the credit card. Sound familiar? It isn’t easy to convince your boss to buy something, whether you’re first starting out with project management tools in the company or you’re looking for a better tool than the one you already have.

convince your boss to say yes

But there’s a secret: it can actually be easy, and even fun, to convince your boss the new tool is what you need. And this technique will work for almost anything, too! New supplies, new hardware, a better office chair…anything. How do you do it? Here goes.

Step One: Building Your Case

The first step in convincing your boss of anything is building your case. Start with a good old-fashioned list of pros and cons, outlining the benefits of the new tool and the drawbacks of the old one. (If you are purchasing a tool for something new, and it isn’t replacing a different one, you just need to focus on the benefits.) You’ll want to put some real research into this – simply saying “this is better!” probably won’t cut it.

You want your pros and cons to speak to the use case of your company, not in general terms. Your boss doesn’t care about the cool Plan vs. Actual feature – but they definitely care about tracking project changes easily, if that’s a pain point for the company. When you build your case, it is crucial you build it around the company – not the tool, or yourself! Therefore, you’ll want to pare down your list to, at most, three to five items for and against, in the context of the organization. Cross off the rest. They won’t help you, they’ll hurt your cause.

In fact, you want this list to address your boss’ concerns. To do that, you’ll need to understand what they are.

Step 1A: Knowing What Your Boss’ Concerns Are

You know why management hates change?

  • Organizations thrive on linear processes and continuity. Things get done when there is a channel for work to flow. Changes to that channel can “upset the apple cart” and affect morale, cohesion, and productivity.
  • Change means shifting focus from what is being done to how it is being done, and work suffers in the short term as a result.
  • Onboarding time is time not worked.
  •  Transitions don’t always work. Managing transitions is a challenge unto itself, and it requires resources.
  • There is a cost to change. Technical problems arise when platforms change. Your tool might save the organization 15% in turnaround time and an additional 15% in costs, but if it requires hiring another IT person, or six months time for everyone to get up to speed on the new tool, you’re actually costing the organization money instead of saving it.

With this in mind, you know the metrics/issues you’ll need to address to convince your boss. Build your case accordingly!

Step Two: Bring People On Board

If you’re going to convince your boss to make a change, you’re going to need to build a certain level of ground support to allay your boss’ fears.

Invite some team members to check out the tool you found. Get their feedback. Do they see the same benefits that you do? If they do, you have something to talk about. If they don’t…your boss’ fears of upsetting the apple cart might be stronger than your idea – however good it is. Once you have their feedback, bring them on board for your plan. “Guys, I am going to talk to Kathryn about this. I want to know if I can count on your support, and mention that we agree on this as a team.”

Step Three: Presenting Your Case

Let’s say, for argument’s sake, your team is using Trello as a project management tool. Trello is a great tool, but it isn’t meeting your needs. You’ve dug around a bit, and tried some other platforms out on the side, and you’ve settled on Proggio. You want to show your case to convince your boss of your conclusions. How would your list of pros and cons look? Perhaps your email would look a little like this:

convince your boss project management tool


As you know, we’ve been struggling recently. The recent round of projects we are handling are more complex and feature more moving parts to track – and we are letting things slip at the margins. Last week we had to scramble Terry and Roberta down to Lisbon for an emergency on-site fix.

I think one change we need to make is with the software we’re using to manage the project. I’ve looked at a few alternatives, and here’s what I found.

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Trello Pros:

  • Kanban board makes workflow easy to assign and monitor
  • Add-on ecosystem means you extend the platform to better fit your needs
  • Collaboration tools are robust

Trello Cons:

  • Lack of a timeline means complex projects are harder to plan, monitor, and manage
  • There are no visual dependencies
  • “To Do” flies under the radar, because all the attention is on “In Progress”

Proggio Pros:

  • Projectmap planning interface is streamlined, promotes visual clarity on project roles and assignments at a glance
  • The platform is built around the team, from design and interface for task management to collaboration tools
  • Portfolio view and reports for management increase transparency and organization integration

Proggio Cons:

  • No app extensions available, less customization opportunity
  • Integrations only available for Zapier, JIRA, and G-Suite
  • more complex than Trello, which could add to onboarding time and learning curve

Both platforms offer strong collaboration tools. Where Trello falls short is in project planning and managing complex projects – and this is something Proggio will help with. Remember the disaster with the McCracken project? We could have avoided that three-week delay with Proggio – that dependency chain we never saw would have been part of the project plan from the start, and everyone would have seen it coming. Same with the Lisbon trip.

Now, I know that Trello is free, and offers a lot for customization options. Proggio will cost us $80-150 per month for our team of ten. But the airfare for Terry and Roberta this past time was $650 alone, and one more time this happens and we’ll have paid the same amount on the year. We aren’t saving money by using the free tool, we’re just spending it elsewhere.

The company is growing and our projects are only getting more complex. There’s already a growing sense of frustration around Trello with the team. Roberta, Kelly, and Peyton all gave Proggio a spin, too, and they agree that this might be the difference-maker for us. I think if you give this a chance, you’ll see it will cut down the time we need to execute projects, and margin costs (like these flights), while increasing team efficiency and morale. Oh, and Proggio’s Portfolio view will give you instant reporting on our project progress, too.

I’d love to hear your thoughts,


Step Four: Follow Up

Your boss is busy. Being a boss is busy work, after all. You might think this tool is mission-critical. It might be, to you. It isn’t to your boss. Your carefully crafted email, with its meticulously built reasoning, may just be ignored. Or banished to a future meeting, yet to be scheduled.

Follow up. In an email, or in person. You don’t want to be too pushy, and you don’t want to come across as disrespectful – it’s a fine line to walk, but success lies on the other side.

Your goal here is to discuss your findings on merit. Whether that is in person (recommended!) or by email, you want to have a conversation that revolves around the benefits gained by making the switch. Your boss will push back, and you will need to ask for the reasoning behind it, too. Maybe the reason your company is using Trello is because the owner’s son is the barista in their offices. Maybe your boss might let your team use your new tool on your own if you can center the opposition to it as an organization-level issue. Hear your boss’ concerns, so that you can better understand the actual issue.

Step Five: Convince Your Boss

You’ve made your list. You’ve got the team on board. You’ve made your presentation. You’ve followed up. Now it’s go time, and it’s showtime.

Call a meeting for the purpose of this discussion. Prepare wisely: You will need to demonstrate the tool to show it does what you’re claiming it does. A small demonstration will work nicely – it will provide a visual to the points you made previously.

Your passion and your belief in the tool are the icing on the cake. The cake itself, though, is a benefit to the organization. You made it the key focus of your presentation for a reason. Make sure you don’t have a one-inch cake and a twelve-foot pile of icing! Proportion is important.

Do this, and your boss will agree. After all, this is something we need.

And then? Pat yourself on the back. You’re the person who made a difference. That’s gotta be good come performance review season…

Postscript: The Proggio Benefits You Want To Focus On In Your Presentation

  • Crystal clear project planning, understandable at a glance by anyone – clear project roles and responsibilities
  • Projects built around the team, not tasks – build momentum towards successful delivery
  • Feature-rich: budget tracking, planned vs actual, team loading, @mentions in project chat, email updates, automatic PPM reporting, and more
  • JIRA integration ends the software silo – allowing full organization integration
  • Increases transparency, giving management a view into every level of the project
  • Pricing: Proggio is just $8-15 per user when paid annually
  • Ease of use: intuitive design means less onboarding time, increased productivity, and a happy team

Helpful Resource: “How To Pitch Your Boss” Infographic

Hat Tip: Rose Leadem, Entrepreneur

convince your boss